Remitly’s CEO Matt Oppenheimer Steps Down After 15 Years: A Deep Dive into His Legacy and Leadership Playbook

In a major shift for one of Seattle’s most prominent fintech success stories, Matt Oppenheimer, the co-founder and longtime CEO of Remitly, has announced he’s stepping down from the CEO role after nearly 15 years at the helm. The remittance giant, which has revolutionized international money transfers for millions of immigrants worldwide, is now transitioning to new leadership under Sebastian Gunningham, a seasoned tech and finance executive who previously led Amazon’s marketplace and payments businesses.

“I feel wonderful, honestly,” Oppenheimer told GeekWire in an exclusive interview. “One thing that has always driven me from the moment I started the business 15 years ago is impact and purpose and doing things with a sense of intentionality. And I feel like that’s how we’ve done this succession planning.”

The Journey From Three-Person Startup to Global Powerhouse

The Remitly story began more than a decade ago when Oppenheimer returned from Kenya, where he was working for Barclays and witnessed firsthand how difficult it was for families to send and receive money across borders. What started as a three-person team at Techstars Seattle has grown into a global remittance platform serving over 9 million people, with revenue of $442.2 million in Q4 2024 alone—a 26% year-over-year increase—and achieving its first full year of GAAP profitability in 2025.

The company went public in 2021 at a valuation of nearly $7 billion, having raised approximately $400 million across multiple funding rounds. But the path to success wasn’t linear. Oppenheimer and his co-founders—Josh Hug and Shivaas Gulati—navigated an early pivot that would prove crucial to their eventual product-market fit.

Oppenheimer’s Leadership Playbook: Lessons from Building Remitly

As he transitions to the role of board chairman, Oppenheimer shared invaluable insights from his journey building Remitly. Here are the key takeaways from his leadership philosophy:

Fall in Love with the Problem, Not Your Product

One of Oppenheimer’s most crucial pieces of advice for entrepreneurs is to focus on the problem you’re solving rather than becoming attached to a specific product solution. “The danger is when founders apply their grit in the wrong place,” he explained. “If they channel that perseverance in the wrong area—the product or trying to force something into existence that customers don’t care about—they fail. They run out of time, energy, or money.”

This mindset allowed Remitly to pivot when necessary. The company initially focused on mobile wallets but shifted to cash pickup, bank deposits, and door-to-door delivery based on customer feedback. “We had to follow customers,” Oppenheimer said. “If we would have been stubborn about only doing mobile wallets—that’s what our pitch said—then we would have failed.”

Get Close to Customers—Even When It Doesn’t Scale

In the early days, Remitly set up a booth at Southcenter Mall near Seattle, outside a legacy remittance location, with nothing more than scotch-taped signage. Oppenheimer referenced a phrase from Airbnb co-founder Brian Chesky: “find marketing channels that don’t scale.” The goal wasn’t growth but insight.

They learned why customers weren’t using Remitly, and that feedback drove their pivotal product pivot. This hands-on approach to understanding customer pain points became a cornerstone of Remitly’s development strategy.

Define Culture as Behaviors—and Keep Rewriting It

Oppenheimer emphasizes that culture isn’t just a list of values posted on a wall. “Culture is how people in a company or institution interact to deliver for their customers,” he said. Before launching their product, the founding team did an offsite to define culture on a whiteboard. Early values like “relationships” were well-intentioned but too broad.

Remitly refreshed its values every six months initially, now every couple of years, evolving them into specific behaviors such as “be a compassionate partner,” “lead authentically,” and “constructively direct.” Customer centricity sits at the top as the single overarching value. The test, Oppenheimer says, is whether values show up in concrete decision-making: “Once you’ve got it defined, [you embed it] into the interview process and the performance review process.”

Find Complementary Co-Founders

Oppenheimer credits much of Remitly’s success to his co-founders. “It’s important for all founders to surround themselves with complementary skills and respect those skills deeply,” he said. While Oppenheimer often cleared obstacles—money transmission licenses, office leases, even taking out the trash—his co-founders brought essential technical and product expertise.

Josh Hug contributed product skills while Shivaas Gulati brought engineering chops. This combination of complementary strengths, united by shared values, created a foundation that could scale from three people to over 3,000 employees.

Raise More Capital Than You Think You Need

Remitly’s fundraising journey involved hundreds of millions of dollars across multiple rounds, none of which were easy. “It requires getting a lot of no’s,” Oppenheimer said. “It requires that grit, tenacity and perseverance that is critical for any entrepreneur to be successful.”

He advises treating fundraising as a two-way conversation, not a one-sided pitch. “Investors can sniff desperation,” he warned. Make sure investors are asking the right questions and consider whether you want them on your board. When the partner is right, Oppenheimer leans toward raising a bit more capital. “Things always take a little bit longer than you imagine,” he said. For companies pursuing bold visions, “if you’ve got the right partner, you can raise enough capital, then it’s worth the dilution to be able to make progress against accomplishing that vision.”

Treat Your Own Growth Like a Product

As Remitly grew from a handful of people to thousands, Oppenheimer built a formal process for his own development as CEO. He started asking each new investor who joined Remitly’s board to run his performance review. “I’d like you to talk to all other board members. I’d like you to talk to my leadership team,” he’d tell them. “And then I’d like your insights.”

He turned that input into a written development plan, shared it with the company, and found coaches and mentors to help work on specific gaps. “It took a lot of intentionality to grow as a leader,” he said. This work continues in his new role as chairman. “After mission and purpose, my second biggest motivator for me personally is growing as a human,” he said. “That’s what I’ve loved about the journey, and it continues in this next role.”

Don’t Underestimate the Role of Community

Seattle has been integral to Remitly’s story. Techstars Seattle helped launch the company (when it was called Beamit Mobile), and talent from the region’s tech ecosystem helped scale it. “The talent we’ve been able to recruit from some of the largest technology companies has been foundational,” Oppenheimer said.

With fewer growth-stage companies in the city than in some other hubs, Oppenheimer believes Remitly could attract people looking to join a mission-driven startup with scale ambitions. Last year, the company moved into a new headquarters in downtown Seattle, and Oppenheimer emphasized their continued commitment to the city. “I want to make sure that’s the case for the next decade to come,” he said.

The Future of Remitly Under New Leadership

As Oppenheimer transitions to chairman, he leaves behind a company that has fundamentally changed how millions of people send money across borders. The mobile technology Remitly developed eliminates many of the forms, codes, and in-person agents traditionally associated with international transfers, making the process faster, cheaper, and more accessible.

Sebastian Gunningham, who takes over as CEO, brings deep experience from Amazon, where he led marketplace and payments businesses. This experience could prove valuable as Remitly continues to expand its services and potentially explore new financial products for its customer base.

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